Chloroacrylophenones and polymers



Patented Feb. 11, 1947 UNITED STATES; *PAT CHLOROACRYLOPHENONES EES POL. 1 Joy G. Lichty, sat, Ohio; assig'nor tof wingfoot v Akron, Ohio, acorporation or l Corporation, Delaware N r win Mammo ram,15

' ..'SerialNo. 460,653

I 2 Claims. te m-cs) @{J-Q' This invention'relates tochloroacrylophenon'es' and, more particularly, toalpha'monochloroacrylophenone and alpha, beta dichloroacrylophenone,their polymers or homopolymers and copolymers.

The new chloroacrylophenones may, be, represented by the followingstructuralformula:

ta t- Cl X in which X is hydrogen or chlorine. The preparation of alpha,beta dichloroacrylo- These productsjwere p0 Duponal is 1 the sodiumusing the above formula and varying the pH phenone is illustrated by thefollowing equation:

' I & C-.C=CH o1o=o-c H01 I A1013 0 c1 c1 H- o1 To 140 grams ofanhydrous AlCla was added 159.5

grams (1 mole) of alpha, beta dichloroacrylyl chloride. The resultingliquid melt was dissolved in 100 cc. of LSz and then 85 grams of benzenewas added drop by drop under anhydrous conditions. HCl gas was given011, and this was swept out with CO2 into aqueous NaOH containing 1 moleof NaOH. Methyl orange indicator showedwhen one mol of HCl was given OE,and

'then ice was added to stop the reaction. Distillation of the benzenelayer gave alpha, beta dichloroacrylophenone with a boiling point of160-161 C./38 mm.

' Using one mol of alpha monochloroacrylyl chloride instead of thedichloroacrylyl chloride in the above example, alphainonochloroacrylophenone is obtained. By using the proper acrylylchloride, anyone. of the following compounds may be obtained:alpha-methyl-beta-chloroacrylophenone, alpha (chloromethyl)acrylophenone, alpha- (chloromethyl) beta-chloroacrylophenone, and

the naphthyl homologues of all of the above-men tioned compounds.

The chloroacrylophenones of this invention can be polymerized; and theycan be copolymeriz'ed with other monomers, such as butadiene, styrene;

isoprene, dimethy1butadiene, 4-methyl 1,3-pentadiene, etc. Thefollowing'example illustrates the polymerization and copolymerization ofthese chloroacrylophenones': Water solution containing 6% Duponol and 2%Vnltamnl no 10 McIlvaines buffers to give the. specified me. cc 10 CC140.48 NaCN 'c 0.5 acetaldehyde c c Butadieneg.- 9.6

Dichloroacrylophenone -..g 6.4

-from 3.7 to 9, 0.133. grams NaBOa as a, 1o-

catalyst, good yields or elastic and extrudable rubber-likeeopolymers'were obtained. :Doubling the sodium borate'and using apH of3.7, a rubber-like'copolymer was likewise obtained. Simi larly,-'usingalpha monochloroacrylophenonewith; I

butadiene,.rubber-like copolymers are obtained.

The ratio of the monomers may be varied from' :10 to 10:90. Using nobutaldiene and 10 grams of either chloroacrylophenone, a rubber-likepolymer of each phenone is obtained. Copolymers are likewise obtained ifinstead or butadiene, one copoiymerizes with butadiene, dimethylbutadiene, 4-methyl 1,3-pentadiene or the like.-

The above examples are merely illustrativeof the invention. For example,it is not necessary to produce the copolymers in an emulsion. If anemulsion is employed, other emulsifying agents, catalysts, etc., may beused. I

What I claim is:

1. Alpha, beta dichloroacrylophenone.

2. The polymerv of alpha, beta-dichloroacrylo- Phenone.

- JOY G. LICHTY. l

I REFERENCES CITED The following references are of recordin the file ofthis patent: I

' "UNITED STATES PA'I'ENTS OTHER REFERENCES I Vbrlander: Chem.Abstracts, vol. 17, p. 1379 (192a); Ber. vol. 56B, pp. 1136-44 (1923)..

Beilsteins: Handbuch der Organ. Chem, Erstes Erganzungswerke 7th-8thvol., 4th ed., 1931, p. 190. (Copyin Div. 6.)

emedifmfa;

saltior lauryl sulfate. Vultamol is a wetting agent. The McIlvainebufias are made by'mixing 0.2 M'disodium phosphate and 0.1 M citricacidsolutions in varying. proportions to vary the pH value. ..Forexample,

